Regioselective Intermolecular [2 + 2]-Cycloaddition of α-Iodo-Unsaturated Ketones Promoted by Diisobutylaluminum Hydride.

نویسندگان

  • Hai-Tao Zhu
  • Sen Ke
  • Ni-Ni Zhou
  • Ming-Jin Fan
  • De-Suo Yang
چکیده

The development of intermolecular [2 + 2]-cycloaddition of α-iodo-unsaturated ketones in the presence of diisobutylaluminum hydride (Dibal-H) is reported to produce various trispirocyclic derivatives containing a cyclobutane ring. This sequential lactonization/[2 + 2]-cycloaddition proceeds in high regioselectivity under mild conditions.

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

منابع مشابه

Regioselective [2+2] and [4+2] cycloaddition reactivity in an asymmetric niobium(bisimido) moiety towards unsaturated organic molecules.

The asymmetric bis-imido structure and the lability of the diethyl ether linkage in complex 1 provide a niobium complex that undergoes regioselective [4+2] cycloaddition reactions with an α,β-unsaturated ketone and cycloaddition reactions that involve bond formation to the MAD ligand (MonoAzabutaDiene). DFT calculations have been used to support an initial azametallacyclobutene intermediate in ...

متن کامل

Copper-catalyzed regioselective synthesis of furan via tandem cycloaddition of ketone with an unsaturated carboxylic acid under air.

A catalytic decarboxylative annulation has been developed for the regioselective synthesis of trisubstituted furans by the cycloaddition of ketones with α,β-unsaturated carboxylic acids under ambient air. A library of furan derivatives were obtained in good yields from the readily available substrates in the combination of a catalytic amount of Cu-salt and a stoichiometric amount of water. Wate...

متن کامل

Investigation on the effect of trifluoromethyl group on the [3+2] cycloadditions of thiocarbonyl S-methanides with α, β-unsaturated ketones: A theoretical study using DFT

A [3+2] cycloaddition (32CA) reaction among a thiocarbonyl ylide (TCY 2) with (E)-4,4,4-trifluoro-4-phenylbut-3-en-2-one (TFB 4) as an electron-deficient enone in tetrahydrofuran (THF) were studied within the Molecular Electron Density Theory (MEDT), at the DFT-B3LYP/6-31G(d) computational level to analysis energetics, selectivities, and mechanistic aspects. The reaction can progress in four co...

متن کامل

Gold-catalyzed regioselective oxidation of propargylic carboxylates: a reliable access to α-carboxy-α,β-unsaturated ketones/aldehydes

Gold-catalyzed intermolecular oxidation of carboxylates of primary or secondary propargylic alcohols are realized with excellent regioselectivity, which is ascribed to inductive polarization of the C-C triple bond by the electron-withdrawing carboxy group. The gold carbene intermediates thus generated undergo selective 1,2-acyloxy migration over a 1,2-C-H insertion, and the selectivities could ...

متن کامل

[4 + 3] Cycloaddition of aromatic α,β-unsaturated aldehydes and ketones with epoxides: one-step approach to synthesize seven-membered oxacycles catalyzed by Lewis acid.

A novel intermolecular [4 + 3] cycloaddition method to construct 1,4-dioxide seven-membered oxacycles was developed. This one-step method was carried out in the presence of catalytic amount of (C(2)H(5))(2)OBF(3) under mild conditions. Seven-membered oxacycles and some natural compounds could be easily synthesized via this protocol. Control experiments were carried out and possible mechanism fo...

متن کامل

ذخیره در منابع من


  با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

عنوان ژورنال:
  • Organic letters

دوره 18 18  شماره 

صفحات  -

تاریخ انتشار 2016